In October 2021 I finally made my first trip to Boston! I planned a trip throughout New England with my mom, and Boston was the first stop for 2 days. Here is my itinerary and details about the trip.
Quick Links
Getting to Boston
Where to Stay in Boston
The Freedom Trail
Eat Italian in the North End
Mike’s Pastry Cannolis
Harvard University
Public Garden
Back Bay Neighborhood
Charles River Esplanade
Additional Recommendations
Final Thoughts
How to get to Boston
Boston Logan International Airport is a major airport and has many flights from all over. I flew on a direct flight from San Diego to Boston on Alaska Airlines.
Where to Stay in Boston
I stayed in an Airbnb in Cambridge near Massachusetts Avenue, which was very safe, walkable, and had lots of great restaurants nearby. Other nice areas to stay are Beacon Hill or Back Bay which are both in Boston.
The metro, called the “T”, is great and can get you just about anywhere. We stayed 10 minutes walking distance to a metro stop, so we opted not to have a car while in Boston. Accommodations in Boston tend to be expensive (coming from a Californian); options in Cambridge may be slightly cheaper.
Day 1 in Boston
Walk the Freedom Trail
On our first day in Boston we walked The Freedom Trail which is a 2.5 mile route that was created to connect 16 historical sites throughout Boston and Charlestown. There is a red brick trail built into the sidewalk to follow, which is awesome because you don’t have to navigate on a map. The trail starts in the Boston Common (park) and ends at Bunker Hill in Charlestown.
Note: the Freedom Trail is not a loop, so plan to backtrack.
This will take a significant portion of the day! I’ve highlighted some of the sites I found most notable below.
Granary Burying Ground (Cemetery)
The Granary Burying Ground is one of Boston’s oldest cemeteries, established in 1660, and is the resting place for historical people such as Paul Revere and John Hancock. Also buried here is much of Benjamin Franklin’s family.
Faneuil Hall Marketplace
Faneuil Hall Marketplace is made up of 3 indoor/ outdoor markets and Faneuil Hall. In present day it is essentially an outdoor mall, however the origin of the marketplace was with the construction of Faneuil Hall in the 1740s as a market and meeting hall. It is said that there were several speeches given in the meeting hall leading up to the Revolutionary War.
Quincy Market was built in the 1820s to provide more market space. There are a ton of great food and shopping options; I ate some tasty clam chowder from Boston Chowda Co.
The Paul Revere House
The Paul Revere House was built in 1680 and is where Paul Revere and his family lived during the Revolutionary War. Despite undergoing renovations over the years, much of the house is original including some furniture.
The house was opened to the public in 1908 and in present day costs $6 (for adults) to go in.
The Paul Revere Mall and Old North Church
The Paul Revere Mall is a plaza with a prominent statue of Paul Revere, several historical plaques, and a large fountain. Behind the plaza is the Old North Church which is where Paul Revere famously lit two lanterns. Two lanterns alerted the American militia that the British were coming by sea, not land, before the battle of Concord and Lexington.
Bunker Hill Monument
The Bunker Hill Monument was first constructed in 1843 to commemorate the Battle of Bunker Hill during the Revolutionary War. The significance of the battle is that despite a British victory, the British lost a significant portion of their troops increasing the American militia’s morale.
Eat Italian Food in the North End
The North End is known for their incredible Italian food. Just about any restaurant you look up has great reviews. We opted to eat at Bricco and ordered the gnocchi and ravioli. It was delicious!
Get Dessert at Mike’s Pastry
Cannolis are really popular in Boston’s North End, especially Mike’s Pastry. There is always a line but it moves fast. Mike’s has a lot of unique flavors that are all top quality, I particularly enjoyed the chocolate mousse and amaretto cannolis.
Day 2 in Boston
Explore Harvard and Cambridge
Harvard is the United State’s oldest university founded in 1636, before the US was independent. The campus is really beautiful with red brick buildings and lots of trees. We didn’t need much time there, but it was neat to check out.
After checking out the campus, we got brunch at Tatte Bakery & Cafe on Massachusetts Avenue which was bustling with students.
Wander through the Public Garden in Boston
After exploring Cambridge, we took the metro into downtown Boston getting off at the Charles/MGH stop in Beacon Hill. From there we wandered through the picturesque neighborhood toward the public garden. We passed Acorn Street which claims to be one of America’s most photographed streets with it’s cobblestone street and red bricks.
The Public Garden is a large park with beautiful vegetation and a pond. In the summer months you can rent boats, and in the winter you can ice skate.
Check Out Boston’s Back Bay Neighborhood
Back Bay is the neighborhood for shopping along Newbury Street. I am not a big shopper, but wanted to check out the area including Copley Square which is a culture-centered plaza. Adjacent to the square is Trinity Church with it’s impressive Romanesque architecture.
Copley Square is also where the Boston Marathon ends. There is a plaque in the square celebrating 100 years.
Ride Bikes Along the Charles River Esplanade
From Back Bay we walked over to the Charles River Esplanade which is a park that spans along the southern bank of the river. We rented Bluebikes, which are Boston’s bike share program, and rode along the bike path.
Along the Esplanade is The Hatch Memorial Shell which is a neat amphitheater built in 1940 and host of many summer concerts. The views of the river are lovely, however it is worth noting that on the other side of the path is a busy road.
Get Dinner in North End (Again)
When in Boston, indulge in Italian food! Yes, we went back to the North End for a second time to eat more Italian food. Night two brought us to Trattoria il Panini where we ordered the Ravioli Porcini, Trombetta al Pesto, Ravioli di Ricotta, and Tortelli Panna e Prosciutto.
Other Things to do in Boston
Get a View at Piers Park
I started and ended my week long trip in New England in Boston, so on the way back to the airport we made a quick stop at Piers Park. This park is across the harbor from Downtown Boston in East Boston toward the airport. The views looking back at the city skyline are awesome!
More Recommendations
In my two days in Boston I felt like I did and saw a lot, but of course there is so much more to do! Here are some other ideas:
Activities
- See a baseball game at Fenway Park
- Visit the historic towns of Concord and Lexington
- Rent a boat on the bay
- Boston Tea Party Ships & Museum
- Museum of Fine Arts
- Samuel Adams Brewery Tour
More Food and Drink Recommendations
- The Friendly Toast
- Ciao Roma
- Citrus and Salt
- Tall Ship
- Downeast Cider House
- Lookout Rooftop at Envoy Hotel
Final Thoughts
I found Boston very walkable and scenic with all the ‘old’ buildings and greenery. My favorite neighborhood was the North End with all the delicious food and charm. Other than a little rain on the first day, the weather was very nice in the high 60s and low 70s. I hope to go back to Boston during another season to get to experience it differently.
After my two days of exploring I decided there are four things that Boston loves: red bricks, Paul Revere, monuments, and Tom Brady.
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